The tower of the ancient castle Torre del Cassero dominates the town. This charismatic town has much to offer any visitor including its beautiful medieval walls, beautiful churches, art treasures and numerous Renaissance structures - e.g. the Loggia by Vasari at the Piazza del Comune.
Castiglion Fiorentino also has many festivals throughout the year including the famous "Palio dei Rioni", a horse race among the three ancient Rioni boroughs of the town Porta Fiorentina, orange-green; Cassero, white-blue; Porta Romana, red-yellow in Piazza Garibaldi, the largest square of the town, held on the 3rd Sunday of June, similar to the Palio of Siena. It includes a colourful and energetic display of the ancient custom of flag-waving - dating back to the 13th century in the weekend preceding the horse race, a spectacular contest between the three groups of flag-wavers is also held. All these are extraordinary shows not to be missed.
A splendid loggia by Vasari looks out onto the beautiful Valle di Chio - or Valle di Dio according to one of the Medici dukes after taking the town for Florence.